Max Bentley’s best years might have been with Chicago, where he won the Hart Trophy in 1946, but at age 27, he was traded to Toronto, where the two-time scoring champion had a lot left to offer.

The Maple Leafs had a lot more talent than Chicago, but Bentley was still a good scorer, posting five consecutive 40-point years with the Buds.  Bentley helped Toronto win three Stanley Cups (1948, 1949 & 1951) and was the leading playoff scorer in 1951.

Bentley was traded to the Rangers before the 1953-54 Season, where he was reunited with his brother Doug, but he only played in half the season, and refused to report to New York the following year.  His rights were given back to Toronto, but they never agreed on terms, and Bentley never played in the NHL again.  As a Maple Leaf, Bentley scored 256 Points, the same amount he did in Chicago.

Bentley was chosen for the Hockey Hall of Fame in 1966.

Max Bentley was not supposed to play in the NHL as the native of Saskatchewan was told by the Montreal Canadiens (who had his rights) that a heart condition would prevent him from being a professional hockey player.

As you can see, the Habs physician was wrong.

The youngest of the Bentley brothers, Max Bentley may have been the most fun to watch. He was one of the best skaters and stickhandlers of his era, and he would often make opponents look foolish with his “dipsy doodle” like play.  Bentley would twice win the NHL scoring title twice while a member of the Chicago Blackhawks and won the Hart Trophy in 1943. Chicago however was not a great team, but he would get traded to the Toronto Maple Leafs and was in a position to provide another a unique skill set to an already loaded team. The fans took to him quickly as he did with the city of Toronto. He would go on to win three Stanley Cups with the Maple Leafs.